N,N-Dimethyltryptamine

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N,N-Dimethyltryptamine (DMT or N,N-DMT) is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine.^[4] DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.^[5]

DMT has a rapid onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a

, making them structural analogs of DMT.

Human consumption

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DMT is produced in many species of plants often in conjunction with its close chemical relatives 5-methoxy-N,N-dimethyltryptamine (

DMT is generally not active orally unless it is combined with a monoamine oxidase inhibitor such as a reversible inhibitor of monoamine oxidase A (RIMA), for example, harmaline.^[5] Without a MAOI, the body quickly metabolizes orally administered DMT, and it therefore has no hallucinogenic effect unless the dose exceeds the body's monoamine oxidase's metabolic capacity. Other means of consumption such as vaporizing, injecting, or insufflating the drug can produce powerful hallucinations for a short time (usually less than half an hour), as the DMT reaches the brain before it can be metabolized by the body's natural monoamine oxidase. Taking an MAOI prior to vaporizing or injecting DMT prolongs and enhances the effects.^[8]

Clinical use research

Existing research on clinical use of DMT mostly focuses on its effects when exogenously administered as a drug. Although the scientific consensus is that DMT is naturally occurring molecule in humans, the effects of endogenous DMT in humans (and more broadly in mammals) is still not well understood.^[13]

Dimethyltryptamine (DMT), an endogenous ligand of

DMT is studied as a potential treatment for Parkinson's disease in a Phase 1/2 clinical trial.^[15]

SPL026 (DMT fumarate) is currently undergoing

Recently, researchers discovered that N,N-dimethyltryptamine is a potent psychoplastogen, a compound capable of promoting rapid and sustained neuroplasticity that may have wide-ranging therapeutic benefit.^[18]

Quantities of dimethyltryptamine and O-methylbufotenin were found present in the cerebrospinal fluid of humans in a psychiatric study.^[19]

Effects

Subjective psychedelic experiences

Subjective experiences of DMT includes profound time-dilatory, visual, auditory, tactile, and proprioceptive distortions and hallucinations, and other experiences that, by most firsthand accounts, defy verbal or visual description.^[20] Examples include perceiving hyperbolic geometry or seeing Escher-like impossible objects.^[21]

Several scientific experimental studies have tried to measure subjective experiences of altered states of consciousness induced by drugs under highly controlled and safe conditions.

Rick Strassman and his colleagues conducted a five-year-long DMT study at the University of New Mexico in the 1990s.^[22] The results provided insight about the quality of subjective psychedelic experiences. In this study participants received the DMT dosage via intravenous injection and the findings suggested that different psychedelic experiences can occur, depending on the level of dosage. Lower doses (0.01 and 0.05 mg/kg) produced some aesthetic and emotional responses, but not hallucinogenic experiences (e.g., 0.05 mg/kg had mild mood elevating and calming properties).^[22] In contrast, responses produced by higher doses (0.2 and 0.4 mg/kg) researchers labeled as "hallucinogenic" that elicited "intensely colored, rapidly moving display of visual images, formed, abstract or both". Comparing to other sensory modalities, the most affected was the visual. Participants reported visual hallucinations, fewer auditory hallucinations and specific physical sensations progressing to a sense of bodily dissociation, as well as to experiences of euphoria, calm, fear, and anxiety.^[22] These dose-dependent effects match well with anonymously posted "trip reports" online, where users report "breakthroughs"^{[clarification needed]} above certain doses.^[23][24][25]

Strassman also stressed the importance of the context where the drug has been taken. He claimed that DMT has no beneficial effects of itself, rather the context when and where people take it plays an important role.^[12][22]

It appears that DMT can induce a state or feeling where the person believes to "communicate with other intelligent lifeforms" (see "machine elves"). High doses of DMT produce a state that involves a sense of "another intelligence" that people sometimes describe as "super-intelligent", but "emotionally detached".^[22]

A 1995 study by Adolf Dittrich and Daniel Lamparter found that the DMT-induced altered state of consciousness (ASC) is strongly influenced by habitual rather than situative factors. In the study, researchers used three dimensions of the APZ questionnaire to examine ASC. The first dimension, oceanic boundlessness (OB), refers to dissolution of ego boundaries and is mostly associated with positive emotions.^[26] The second dimension, anxious ego-dissolution (AED), represents a disordering of thoughts and decreases in autonomy and self-control. Last, visionary restructuralization (VR) refers to auditory/visual illusions and hallucinations.^[27] Results showed strong effects within the first and third dimensions for all conditions, especially with DMT, and suggested strong intrastability of elicited reactions independently of the condition for the OB and VR scales.^[26]

Reported encounters with external entities

Entities perceived during DMT inebriation have been represented in diverse forms of psychedelic art. The term machine elf was coined by ethnobotanist

The medieval Jewish philosophers whom I rely upon for understanding the Hebrew Bible text and its concept of prophecy portray angels as God's intermediaries. That is, they perform a certain function for God. Within the context of my DMT research, I believe that the beings that volunteers see could be conceived of as angelic – that is, previously invisible, incorporeal spiritual forces that are engarbed or enclothed in a particular form – determined by the psychological and spiritual development of the volunteers – bringing a particular message or experience to that volunteer.^[32]

Strassman's experimental participants also note that some other entities can subjectively resemble creatures more like insects and aliens.^[33] As a result, Strassman writes these experiences among his experimental participants "also left me feeling confused and concerned about where the spirit molecule was leading us. It was at this point that I began to wonder if I was getting in over my head with this research."^[34]

Hallucinations of strange creatures had been reported by Stephen Szara in a 1958 study in psychotic patients, in which he described how one of his subjects under the influence of DMT had experienced "strange creatures, dwarves or something" at the beginning of a DMT trip.^[35][36]

Other researchers of the entities seemingly encountered by DMT users describe them as "entities" or "beings" in humanoid as well as animal form, with descriptions of "little people" being common (non-human

Likening them to descriptions of rattling and chattering auditory phenomena described in encounters with the Hayyoth in the Book of Ezekiel, Rick Strassman notes that participants in his studies, when reporting encounters with the alleged entities, have also described loud auditory hallucinations, such as one subject reporting typically "the elves laughing or talking at high volume, chattering, twittering".^[31]

Near-death experience

A 2018 study found significant relationships between a DMT experience and a near-death experience (NDE).^[41] A 2019 large-scale study pointed that ketamine, Salvia divinorum, and DMT (and other classical psychedelic substances) may be linked to near-death experiences due to the semantic similarity of reports associated with the use of psychoactive compounds and NDE narratives, but the study concluded that with the current data it is neither possible to corroborate nor refute the hypothesis that the release of an endogenous ketamine-like neuroprotective agent underlies NDE phenomenology.^[42]

Physiological response

According to a dose-response study in human subjects, dimethyltryptamine administered

Unlike other classical psychedelics, studies report that DMT did not exhibit tolerance upon repeated administration of twice a day sessions, separated by 5 hours, for 5 consecutive days; field reports suggests a refractory period of only 15 to 30 minutes, while the plasma levels of DMT was nearly undetectable 30 minutes after intravenous administration.^[55] Another study of four closely spaced DMT infusion sessions with 30 minute intervals also suggests no tolerance buildup to the psychological effects of the compound, while heart rate responses and neuroendocrine effects were diminished with repeated administration.^[55] A fully hallucinogenic dose of DMT did not demonstrate cross-tolerance to human subjects who are highly tolerant to LSD;^[56] researches suggest that DMT exhibits unique pharmacological properties compared to other classical psychedelics.^[55]

Long-term use

There have been no serious adverse effects reported on long-term use of DMT, apart from acute cardiovascular events.^[52] Repeated and one-time administration of DMT produces marked changes in the cardiovascular system,^[52] with an increase in systolic and diastolic blood pressure; although the changes were not statistically significant, a robust trend towards significance was observed for systolic blood pressure at high doses.^[57]

Drug-interactions

DMT is inactive when ingested orally due to metabolism by

DMT is broken down by the enzyme

Naturally occurring substances (of both vegetable and animal origin) containing DMT have been used in South America since pre-Columbian times.^[68][69]

DMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske.

In terms of a scientific understanding, the hallucinogenic properties of DMT were not uncovered until 1956 by Hungarian chemist and psychiatrist Stephen Szara. In his paper "Dimethyltryptamin: Its Metabolism in Man; the Relation of its Psychotic Effect to the Serotonin Metabolism", Szara employed synthetic DMT, synthesized by the method of Speeter and Anthony, which was then administered to 20 volunteers by intramuscular injection. Urine samples were collected from these volunteers for the identification of DMT metabolites.^[77] This is considered to be the converging link between the chemical structure DMT to its cultural consumption as a psychoactive and religious sacrament.^[78]

Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine

freebase form, although less stable than DMT hemifumarate, is favored by recreational users choosing to vaporize the chemical as it has a lower boiling point.^[106]

Biosynthesis

Dimethyltryptamine is an

N-methyltryptamine (NMT).^[108][109] NMT is in turn transmethylated by the same process (step 3) to form the end product N,N-dimethyltryptamine. Tryptamine transmethylation is regulated by two products of the reaction: SAH,^{[110][111][112]} and DMT^[110][112]

were shown ex vivo to be among the most potent inhibitors of rabbit INMT activity.

This transmethylation mechanism has been repeatedly and consistently proven by

radiolabeling of SAM methyl group with carbon-14 ((¹⁴C-CH₃)SAM).^{[108][110][112][113][114]}

Laboratory synthesis

DMT can be synthesized through several possible pathways from different starting materials. The two most commonly encountered synthetic routes are through the reaction of

beta-carboline byproducts of unknown toxicity while using sodium borohydride in absence of acid does not.^[117] Bufotenine, a plant extract, can also be synthesized into DMT.^[118]

Alternatively, an excess of

quaternary ammonium salt, which is then dequaternized (demethylated) in ethanolamine to yield DMT. The same two-step procedure is used to synthesize other N,N-dimethylated compounds, such as 5-MeO-DMT.^[119]

Clandestine manufacture

In a clandestine setting, DMT is not typically synthesized due to the lack of availability of the starting materials, namely tryptamine and oxalyl chloride. Instead, it is more often extracted from plant sources using a nonpolar hydrocarbon solvent such as naphtha or heptane, and a base such as sodium hydroxide.^{[citation needed]}

Alternatively, an

acid-base extraction

is sometimes used instead.

A variety of plants contain DMT at sufficient levels for being viable sources,^[4] but specific plants such as Mimosa tenuiflora, Acacia acuminata and Acacia confusa are most often used.

The chemicals involved in the extraction are commonly available. The plant material may be illegal to procure in some countries. The end product (DMT) is illegal in most countries.

Evidence in mammals

Published in Science in 1961, Julius Axelrod found an N-methyltransferase enzyme capable of mediating biotransformation of tryptamine into DMT in a rabbit's lung.^[108] This finding initiated a still ongoing scientific interest in endogenous DMT production in humans and other mammals.^[109][45] From then on, two major complementary lines of evidence have been investigated: localization and further characterization of the N-methyltransferase enzyme, and analytical studies looking for endogenously produced DMT in body fluids and tissues.^[109]

In 2013, researchers reported DMT in the pineal gland microdialysate of rodents.^[120]

A study published in 2014 reported the biosynthesis of N,N-dimethyltryptamine (DMT) in the human melanoma cell line SK-Mel-147 including details on its metabolism by peroxidases.^[121] It is assumed that more than half of the amount of DMT produced by the acidophilic cells of the pineal gland is secreted before and during death,^{[citation needed]} the amount being 2.5–3.4 mg/kg. However, this claim by Strassman has been criticized by David Nichols who notes that DMT does not appear to be produced in any meaningful amount by the pineal gland. Removal or calcification of the pineal gland does not induce any of the symptoms caused by removal of DMT. The symptoms presented are consistent solely with reduction in melatonin, which is the pineal gland's known function. Nichols instead suggests that dynorphin and other endorphins are responsible for the reported euphoria experienced by patients during a near-death experience.^[122] In 2014, researchers demonstrated the immunomodulatory potential of DMT and 5-MeO-DMT through the Sigma-1 receptor of human immune cells. This immunomodulatory activity may contribute to significant anti-inflammatory effects and tissue regeneration.^[123]

Endogenous DMT

N,N-Dimethyltryptamine (DMT), a psychedelic compound identified endogenously in mammals, is biosynthesized by aromatic L-amino acid decarboxylase (AADC) and indolethylamine-N-methyltransferase (INMT). Studies have investigated brain expression of INMT transcript in rats and humans, coexpression of INMT and AADC mRNA in rat brain and periphery, and brain concentrations of DMT in rats. INMT transcripts were identified in the cerebral cortex, pineal gland, and choroid plexus of both rats and humans via in situ hybridization. Notably, INMT mRNA was colocalized with AADC transcript in rat brain tissues, in contrast to rat peripheral tissues where there existed little overlapping expression of INMT with AADC transcripts. Additionally, extracellular concentrations of DMT in the cerebral cortex of normal behaving rats, with or without the pineal gland, were similar to those of canonical monoamine neurotransmitters including serotonin. A significant increase of DMT levels in the rat visual cortex was observed following induction of experimental cardiac arrest, a finding independent of an intact pineal gland. These results show for the first time that the rat brain is capable of synthesizing and releasing DMT at concentrations comparable to known monoamine neurotransmitters and raise the possibility that this phenomenon may occur similarly in human brains.^[124]

The first claimed detection of mammalian

endogenous DMT was published in June 1965: German researchers F. Franzen and H. Gross report to have evidenced and quantified DMT, along with its structural analog bufotenin (5-HO-DMT), in human blood and urine.^[125] In an article published four months later, the method used in their study was strongly criticized, and the credibility of their results challenged.^[126]

Few of the analytical methods used prior to 2001 to measure levels of endogenously formed DMT had enough sensitivity and selectivity to produce reliable results.

limit of detection

; n = number of samples; ng/L and ng/kg = nanograms (10⁻⁹ g) per litre, and nanograms per kilogram, respectively):

DMT in body fluids and tissues (NB: units have been harmonized)

Species	Sample	Results
Human	Blood serum	< LOD (n = 66)[45]
	Blood plasma	< LOD (n = 71)[45]  ♦  < LOD (n = 38); 1,000 & 10,600 ng/L (n = 2)[130]
	Whole blood	< LOD (n = 20); 50–790 ng/L (n = 20)[131]
	Urine	< 100 ng/L (n = 9)[45]  ♦  < LOD (n = 60); 160–540 ng/L (n = 5)[128]  ♦  Detected in n = 10 by GC-MS[132]
	Feces	< 50 ng/kg (n = 12); 130 ng/kg (n = 1)[45]
	Kidney	15 ng/kg (n = 1)[45]
	Lung	14 ng/kg (n = 1)[45]
	Lumbar CSF	100,370 ng/L (n = 1); 2,330–7,210 ng/L (n = 3); 350 & 850 ng/L (n = 2)[46]
Rat	Kidney	12 & 16 ng/kg (n = 2)[45]
	Lung	22 & 12 ng/kg (n = 2)[45]
	Liver	6 & 10 ng/kg (n = 2)[45]
	Brain	10 & 15 ng/kg (n = 2)[45]  ♦  Measured in synaptic vesicular fraction[47]
Rabbit	Liver	< 10 ng/kg (n = 1)[45]

A 2013 study found DMT in microdialysate obtained from a rat's pineal gland, providing evidence of endogenous DMT in the mammalian brain.^[120] In 2019 experiments showed that the rat brain is capable of synthesizing and releasing DMT. These results raise the possibility that this phenomenon may occur similarly in human brains.^[49]

Detection in body fluids

DMT may be measured in blood, plasma or urine using chromatographic techniques as a diagnostic tool in clinical poisoning situations or to aid in the medicolegal investigation of suspicious deaths. In general, blood or plasma DMT levels in recreational users of the drug are in the 10–30 μg/L range during the first several hours post-ingestion.^{[citation needed]} Less than 0.1% of an oral dose is eliminated unchanged in the 24-hour urine of humans.^{[133][134][clarification needed]}

INMT

Before techniques of

reverse isotope dilution analysis coupled to mass spectrometry for rabbit^[135][136] and human^[137]

lung during the early 1970s.

Selectivity rather than sensitivity proved to be a challenge for some TLC methods with the discovery in 1974–1975 that incubating rat blood cells or brain tissue with (¹⁴C-CH₃)SAM and NMT as substrate mostly yields tetrahydro-β-carboline derivatives,[109]^[110][138] and negligible amounts of DMT in brain tissue.^[109] It is indeed simultaneously realized that the TLC methods used thus far in almost all published studies on INMT and DMT biosynthesis are incapable to resolve DMT from those tetrahydro-β-carbolines.^[109] These findings are a blow for all previous claims of evidence of INMT activity and DMT biosynthesis in avian^[139] and mammalian brain,^[140][141] including in vivo,^[142][143] as they all relied upon use of the problematic TLC methods:^[109] their validity is doubted in replication studies that make use of improved TLC methods, and fail to evidence DMT-producing INMT activity in rat and human brain tissues.^[144][145] Published in 1978, the last study attempting to evidence in vivo INMT activity and DMT production in brain (rat) with TLC methods finds biotransformation of radiolabeled tryptamine into DMT to be real but "insignificant".^[146] Capability of the method used in this latter study to resolve DMT from tetrahydro-β-carbolines is questioned later.^[110]

To localize INMT, a qualitative leap is accomplished with use of modern techniques of

in-situ hybridization, a far more accurate tool than the northern blot analysis, found mRNA coding for INMT expressed in the human cerebral cortex, choroid plexus, and pineal gland.^[49]

Pharmacology

Pharmacokinetics

DMT peak level concentrations (C_max) measured in whole blood after intramuscular (IM) injection (0.7 mg/kg, n = 11)[148] and in plasma following intravenous (IV) administration (0.4 mg/kg, n = 10)^[22] of fully psychedelic doses are in the range of around 14 to 154 μg/L and 32 to 204 μg/L, respectively. The corresponding molar concentrations of DMT are therefore in the range of 0.074–0.818 μmol/L in whole blood and 0.170–1.08 μmol in plasma. However, several studies have described active transport and accumulation of DMT into rat and dog brains following peripheral administration.^{[149][150][151][152][153]} Similar active transport, and accumulation processes likely occur in human brains and may concentrate DMT in brain by several-fold or more (relatively to blood), resulting in local concentrations in the micromolar or higher range. Such concentrations would be commensurate with serotonin brain tissue concentrations, which have been consistently determined to be in the 1.5–4 μmol/L range.^[154][155]

Closely coextending with peak psychedelic effects, mean time to reach peak concentrations (T_max) was determined to be 10–15 minutes in whole blood after IM injection,

freeze-dried ayahuasca gel caps, DMT T_max is considerably delayed: 107.59 ± 32.5 minutes,^[156] and 90–120 minutes,^[157]

respectively. The pharmacokinetics for vaporizing DMT have not been studied or reported.

Neurogenesis

See also: 5-MeO-DMT § Neurogenesis, Ayahuasca § Neurogenesis, and Banisteriopsis caapi § Neurogenesis

In September 2020, an in vitro and in vivo study showed that DMT present in the ayahuasca infusion promotes neurogenesis.^[158]

Pharmacodynamics

DMT binds non-

serotonin receptors: 5-HT_1A,^{[159][160][161]} 5-HT_1B,^[159][162] 5-HT_1D,^{[159][161][162]} 5-HT_2A,^{[159][161][162][163]} 5-HT_2B,^[159][162] 5-HT_2C,^{[159][162][163]} 5-HT₆,^[159][162] and 5-HT₇.^[159][162] An agonist action has been determined at 5-HT_1A,^[160] 5-HT_2A and 5-HT_2C.^{[159][162][163]} Its efficacies at other serotonin receptors remain to be determined. Of special interest will be the determination of its efficacy at human 5-HT_2B receptor as two in vitro assays evidenced DMT's high affinity for this receptor: 0.108 µmol/L^[162] and 0.184 µmol/L.^[159] This may be of importance because chronic or frequent uses of serotonergic drugs showing preferential high affinity and clear agonism at 5-HT_2B receptor have been causally linked to valvular heart disease.^{[164][165][166]}

It has also been shown to possess affinity for the

substrate for the cell-surface serotonin transporter (SERT) expressed in human platelets, and the rat vesicular monoamine transporter 2 (VMAT2), which was transiently expressed in fall armyworm Sf9 cells. DMT inhibited SERT-mediated serotonin uptake into platelets at an average concentration of 4.00 ± 0.70 µmol/L and VMAT2-mediated serotonin uptake at an average concentration of 93 ± 6.8 µmol/L.^[169]

As with other so-called "classical hallucinogens",

functionally selective activation of the 5-HT_2A receptor.^{[22][159][171][172][173][174][175]} DMT concentrations eliciting 50% of its maximal effect (half maximal effective concentration = EC₅₀) at the human 5-HT_2A receptor in vitro are in the 0.118–0.983 µmol/L range.^{[159][162][163][176]} This range of values coincides well with the range of concentrations measured in blood and plasma after administration of a fully psychedelic dose (see Pharmacokinetics

).

As DMT has been shown to have slightly better efficacy (EC₅₀) at human serotonin 2C receptor than at the 2A receptor,[162]^[163] 5-HT_2C is also likely implicated in DMT's overall effects.^[172][177] Other receptors such as 5-HT_1A^{[161][172][174]} and σ₁^[168][178] may also play a role.

In 2009, it was hypothesized that DMT may be an

endogenous ligand for the σ₁ receptor.^[168][178] The concentration of DMT needed for σ₁ activation in vitro (50–100 µmol/L) is similar to the behaviorally active concentration measured in mouse brain of approximately 106 µmol/L^[179] This is minimally 4 orders of magnitude higher than the average concentrations measured in rat brain tissue or human plasma under basal conditions (see Endogenous DMT), so σ₁ receptors are likely to be activated only under conditions of high local DMT concentrations. If DMT is stored in synaptic vesicles,^[169] such concentrations might occur during vesicular release. To illustrate, while the average concentration of serotonin in brain tissue is in the 1.5–4 µmol/L range,^[154][155] the concentration of serotonin in synaptic vesicles was measured at 270 mM.^[180]

Following vesicular release, the resulting concentration of serotonin in the synaptic cleft, to which serotonin receptors are exposed, is estimated to be about 300 µmol/L. Thus, while in vitro receptor binding affinities, efficacies, and average concentrations in tissue or plasma are useful, they are not likely to predict DMT concentrations in the vesicles or at synaptic or intracellular receptors. Under these conditions, notions of receptor selectivity are moot, and it seems probable that most of the receptors identified as targets for DMT (see above) participate in producing its psychedelic effects.

Binding sites	Binding affinity Ki (μM)[181]
5-HT1A	0.075
5-HT2A	0.237
5-HT2C	0.424
D1	6
D2	3
D3	6.3
α1A	1.3
α2A	2.1
TAAR1	2.2
H1	0.22
SERT	6
DAT	22
NET	6.5

Society and culture

Black market

Electronic cigarette cartridges filled with DMT started to be sold on the black market in 2018.^[182]

See also

• Dimethyltryptamine-N-oxide
• Psychedelic drug
• List of psychoactive plants
• MPMI
• Serotonergic psychedelic
• Psychoplastogen
• Alexander Shulgin
• SN-22
• Rick Strassman

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External links

Wikimedia Commons has media related to Dimethyltryptamine.

• DMT chapter from TiHKAL